10-[4-[[4-(cis-4,7,10,13,16,19-docosahexenoyl)amino]benzyl]-1-piperazino]carbonyloxy-camptothecin

Base Information

• Chemical Name: 10-[4-[[4-(cis-4,7,10,13,16,19-docosahexenoyl)amino]benzyl]-1-piperazino]carbonyloxy-camptothecin
• CAS No.: 656233-43-1
• Molecular Formula: C₅₄H₆₁N₅O₇
• Molecular Weight: 892.108
• Mol file: 656233-43-1.mol

Synonyms:10-[4-[[4-(cis-4,7,10,13,16,19-docosahexenoyl)amino]benzyl]-1-piperazino]carbonyloxy-camptothecin

Chemical Property of 10-[4-[[4-(cis-4,7,10,13,16,19-docosahexenoyl)amino]benzyl]-1-piperazino]carbonyloxy-camptothecin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 10-[4-[[4-(cis-4,7,10,13,16,19-docosahexenoyl)amino]benzyl]-1-piperazino]carbonyloxy-camptothecin

There total 6 articles about 10-[4-[[4-(cis-4,7,10,13,16,19-docosahexenoyl)amino]benzyl]-1-piperazino]carbonyloxy-camptothecin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

1-[4-(cis-4,7,10,13,16,19-docosahexenoyl)amino]benzylpiperazine (656233-41-9) + 4-nitrophenyl camptothecin-10-yl carbonate (656233-42-0) → 10-[4-[[4-(cis-4,7,10,13,16,19-docosahexenoyl)amino]benzyl]-1-piperazino]carbonyloxy-camptothecin (656233-43-1)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1016/j.bmc.2005.06.039

Reference yield:

1-bromomethyl-4-nitro-benzene (100-11-8) → 10-[4-[[4-(cis-4,7,10,13,16,19-docosahexenoyl)amino]benzyl]-1-piperazino]carbonyloxy-camptothecin (656233-43-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / potassium carbonate / dimethylformamide / 4 h / 20 °C

2: 97 percent / H₂ / Pd/C / ethyl acetate / 2 h

3: 73 percent / 2-(1-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium*PF₆; N,N-diisopropylethylamine / acetonitrile

4: 90 percent / HCl / ethyl acetate / 0.5 h / 20 °C

5: 72 percent / triethylamine / tetrahydrofuran / 2 h / 20 °C

With hydrogenchloride; hydrogen; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmc.2005.06.039

Reference yield:

1-[(4-nitrophenyl)methyl]-4-tert-butyloxycarbonylpiperazine (130636-61-2) → 10-[4-[[4-(cis-4,7,10,13,16,19-docosahexenoyl)amino]benzyl]-1-piperazino]carbonyloxy-camptothecin (656233-43-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / H₂ / Pd/C / ethyl acetate / 2 h

2: 73 percent / 2-(1-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium*PF₆; N,N-diisopropylethylamine / acetonitrile

3: 90 percent / HCl / ethyl acetate / 0.5 h / 20 °C

4: 72 percent / triethylamine / tetrahydrofuran / 2 h / 20 °C

With hydrogenchloride; hydrogen; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; acetonitrile;

DOI:10.1016/j.bmc.2005.06.039

upstream raw materials:

1-[4-(cis-4,7,10,13,16,19-docosahexenoyl)amino]benzylpiperazine

4-nitrophenyl camptothecin-10-yl carbonate

tert-butyl 4-[4-(cis-4,7,10,13,16,19-docosahexenoyl)amino]benzyl-1-piperazinecarboxylate

(S)-10-hydroxycamptothecin

Refernces

• 1、 -. "Novel anticancer conjugates of camptothecin and unsaturated fatty acids". Page/Page column 12-13; Sheet 2. . Retrieved 2008/06/13.